End-of-Year Game Plan

This essay initially appeared in the Monday morning newsletter on 10/21/24.

Friends, it is time. 

It’s late October. Halloween is a week from Thursday. Before we know it, we’ll blink and it’ll be Christmas.

These are the kinds of thoughts that start swirling around in my head this time of year.

And I know it’s not just me! Over the past week, I’ve had similar conversations with a couple of different people. We all expressed feelings of overwhelm and not having a good grasp of what’s coming up for the rest of the year. Our minds feel too full.

If we’re feeling like that, I thought there might be a chance you are too. 

So, it is time. It is time for the very important ** end-of-year game plan session **. 

Here’s the thing: the next two and a half months are wonderful, and magical, and a great time of year. But it’s also a lot! There’s a lot of extra stuff piled onto already full plates.

Because of that, I think it’s even more crucial to enter this season with intention. Deciding what matters most and going all in, and conversely, naming what you’ll deprioritize or drop for this year.

How? 

Enter: the end-of-year game plan session.

This session is partially inspired by my own trial and errors over the years and partially inspired by the book I’m reading right now (The Plan by Kendra Adachi, which is a wonderful book all about compassionate time management – love that!). 

In total, there are five steps. But this is more of a Choose Your Own Adventure vs. prescriptive method. Personally, I find it helpful to do the five steps over a couple of days, but you may decide one step stands out more than the others. You do you!

For me, the goal of this session is to organize and make sense of the tasks and to-dos in my head, helping myself feel calmer, more grounded and more able to enjoy and appreciate the time right in front of me. This session doesn’t have to be tied to holidays, but this is usually the time of year I find myself needing some extra help to organize my thoughts.

Lastly, why not make this fun? If the below intrigues you, think about what you want your experience to be like. Maybe you do a few steps this morning with your coffee and a seasonal candle burning. Or, maybe you bookmark this for later and work through the below with a cocktail and some upbeat music. Remember, this can be fun and enjoyable. 

Okay, without further ado, let’s get into it!

The End-Of-Year Game Plan Session 

Step 1: Print out blank monthly calendars and add known activities and events to them. 

I like the website https://print-a-calendar.com/. Print out monthly calendars for the next couple of months and start writing in what you know is coming up. Look up your flight times, double check someone’s birthday and just get all of it onto paper. 

Digital calendars are great, but I think there is something really helpful – especially this time of year – about seeing everything physically in front of you. 

That’s it! That’s Step 1. 

Step 2: Brain dump and write down what’s on your mind regarding end-of-year plans.

What is causing your brain to feel full and overwhelmed? Take a fresh piece of paper and just start writing. It doesn’t have to make sense or be logical just yet. Jot down random to-dos nagging you, things that don’t have a plan yet, or things you know you want to do before end-of-year. Reference your monthly calendars in front of you and see if they spark anything to write down. 

When I did this, I found it helpful to have separate lists going. I had one list for “life,” one list for “wedding” and one list for “work.” With my monthly calendars and three pieces of paper spread in front of me, I let my mind wander and captured tasks on the appropriate piece of paper.

After you are done with Step 2, you may consider taking a break before moving onto the next step. Personally, I found it helpful to walk away from my brain dump list for a day to give myself a beat and to see if any other items surfaced that needed to be added to the list. 

Step 3: Decide what matters and what can be easier. 

I love this next step. This step comes directly from Kendra Adachi and the “Lighten the Load” framework she outlines in her book The Plan. 

Kendra writes, “If you don’t practice naming what matters, by default you’ll try to make everything matter. That is one of the many reasons you are so very tired. Instead of trying to do everything that’s now visible, name what is most important. That way you can organize your time according to what matters most.” 

I like to take two different colored highlighters and designate one as the sign for ‘make it matter’ and other as the sign for ‘make it easier.’  Then, go back through your brain dump list and assign significance to each item: What matters to you in this season? What do you want to make easier? Highlight or markup your lists accordingly. 

Step 4: Figure out decisions and to-dos. 

By now you have corralled all the swirling thoughts in your head AND assigned significance to them. Yay! I hope you already feel better. 

Now, we are going to get even granular and for each thing you wrote down, figure out: 1) what do you need to decide and 2) what do you need to do? 

Grab another piece of paper and reference your brain dump. Starting with the things you designated as “This matters this season,” think about what you need to do. 

For example, “holiday gift giving” was on my brain dump list and something I noted as mattering for this season. I love the experience of gift giving during the holidays. But honestly, at the start of this session, the idea of “gift giving” felt stressful because I didn’t have a plan and I didn’t know what to do first.

When I transferred “holiday gift giving” from my brain dump list to my new list, I started to write the following decisions and to-dos under it:

• Make a gift giving spreadsheet
• Start thinking about gifts to give before Black Friday sales
• Shop for gifts during Black Friday
• Dedicate a night in early December to wrapping gifts while watching a Christmas movie

No wonder I was initially stressed out by “holiday gift giving!” The phrase really represents four steps that I wasn’t considering.

Go through your brain dump list, starting with the things you’ve designated as mattering, and ask yourself 1) what do you need to decide and 2) what do you need to do? Jot this all down on a new piece of paper. 

After you get through the things that matter, do the same for the things you’ve designated as “make easier for this season.” For those, think about how you can take some of the pressure off. Maybe note you’ll ask someone for help? Maybe make a decision in advance? 

Break all your items down into actions and individual decisions and then you’ll be ready for our final step. 

Step 5: Map your decisions and actions by urgency. 

Now, we organize! This process is similar to a closet clean out. So far, we’ve pulled out all our clothes, dumped them onto our bed and sorted through what to keep, donate and toss. Now, it’s time to put everything you’re keeping back into your – hopefully simplified and more streamlined – closet that’s going to make getting dressed so much easier. 

This again comes from Kendra’s Lighten the Load framework. We are going to assign urgency to each of the tasks you identified in the prior step. 

On yet another piece of paper (promise this is the last one!), draw a vertical and then horizontal line to divide the page into four quadrants. Assign each of the four quadrants to one of the following: Now, Soon, Later, Delegate. 

Then, start plotting your decisions and to-dos from the previous step accordingly. For example,  I put “create gift giving spreadsheet” into my Nowquadrant (I’m doing that this week), “think about gifts to give” into Soon and “buy gifts” and “wrap gifts” in Later (I’m going to shop during Black Friday sales and wrap presents in December).

This identified which decisions I need to make and what I need to do this week, while also keeping future decisions and tasks documented for later.

My plan is to continue referencing my quadrants at the start of each week, crossing off tasks and picking new ones accordingly as we move through the rest of the year. This feels SO much better than having tasks floating around in mind and feeling like I should be cramming to-dos into any free moment.

And that’s it! If you try this, I’d love to know if you found it helpful. Or, if you have another way to plan for busy seasons, I’d love to know that too!

Remember, no matter what, you are doing great. Anything that helps you feel calmer and able to move through this season with more ease and enjoyment is worth it.

Hope you have a great week!!